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Generated: December 13, 2017

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Title: Lactams and processes for stereoselective enrichment of lactams, amides, and esters
Abstract:Novel lactams and processes for the preparation of chiral compounds having utility as intermediates in the synthesis of compounds with Central Nervous System stimulant activity.
Inventor(s): Zeitlin; Andrew L. (Millington, NJ), Stirling; David I. (Branchburg, NJ)
Assignee: Celgene Corporation (Warren, NJ)
Filing Date:Jan 05, 1996
Application Number:08/583,317
Claims:1. A process for producing d-threo-2-(piperid-2-yl)-2-phenyl acetic acid comprising bringing a compound of the formula (I): ##STR3## wherein R.sup.1 and R.sup.2 are hydrogen, and R.sup.3 is carbamoyl into contact with an amidase at least until a substantial amount of said compound is converted to d-threo-2-(piperid-2-yl)-2-phenyl acetic acid substantially free of the 1-isomer, and recovering said d-threo-2-(piperid-2-yl)-2-phenyl acetic acid or a derivative thereof.

2. The process according to claim 1 wherein the amidase is of microbial origin.

3. The process according to claim 2 wherein the amidase is obtained from a microorganism selected from the group consisting of Alcaligenes, Pseudomonas, Rhodopseudomonas, Corynebacterium, Escherichia, Arthrobacter, Aspergillus, Acinetobacter, Brevibacterium, Bacillus, Mycobacterium, Rhodococcus, Agrobacterium, Botrytis, Candida, Chaetomium, Chromobacterium, Cladosporium, Enterobacter, Microbacterium, Mucor, Nocardia, Ophiobolus, Penicillium, Rhizopus, Rhodotorula, Saccharomyces, Staphylococcus, Streptomyces, Torulopsis, and Trichoderma.

4. The process according to claim 1 wherein the unreacted amide is recovered.

5. A process for producing d-threo-2- (piperid-2-yl) -2-phenyl acetic acid comprising bringing a compound of the formula (I): ##STR4## wherein R.sup.1 and R.sup.3 taken together are carbonyl, and R.sup.2 is hydrogen into contact with at least one of an amidase or lactamase at least until a substantial amount of said compound is converted to d-threo-2-(piperid-2-yl)-2-phenyl acetic acid substantially free of the 1-isomer, and recovering said d-threo-2-(piperid-2-yl)-2-phenyl acetic acid or a derivative thereof.

6. The process according to claim 5 wherein the amidase or lactamase is of microbial origin.

7. The process according to claim 6 wherein the amidase or lactamase is obtained from a microorganism selected from the group consisting of Alcaligenes, Pseudomonas, Rhodopseudomonas, Corynebacterium, Escherichia, Arthrobacter, Aspergillus, Acinetobacter, Brevibacterium, Bacillus, Mycobacterium, Rhodococcus, Agrobacterium, Botrytis, Candida, Chaetomium, Chromobacterium, Cladosporium, Enterobacter, Microbacterium, Mucor, Nocardia, Ophiobolus, Penicillium, Rhizopus, Rhodotorula, Saccharomyces, Staphylococcus, Streptomyces, Torulopsis, and Trichoderma, or preparations thereof.

8. The process according to claim 5 wherein the unreacted (d)-trans-7-phenyl-1-azabicyclo(4,2,0)-octan-8-one is recovered.

9. A process for producing d-threo-2-(piperid-2-yl)-2-phenyl acetic acid comprising bringing a compound of the formula (I): ##STR5## wherein R.sup.3 is cyano, R.sup.1 and R.sup.2 are hydrogen, into contact with a nitrilase at least until a substantial amount of said compound is converted to d-threo-2-(piperid-2-yl)-2-phenyl acetic acid substantially free of the 1-isomer, and recovering said d-threo-2-(piperid-2-yl)-2-phenyl acetic acid or a derivative thereof.

10. The process according to claim 9 wherein the nitrilase is of microbial origin.

11. The process according to claim 10 wherein the nitrilase is obtained from a microorganism selected from the group consisting of Alcaligenes, Pseudomonas, Rhodopseudomonas, Corynebacterium, Escherichia, Arthrobacter, Aspergillus, Acinetobacter, Brevibacterium, Bacillus, Mycobacterium, Rhodococcus , Agrobacterium, Botrytis , Candida, Chaetomium, Chromobacterium, Cladosporium, Enterobacter, Microbacterium, Mucor, Nocardia, Ophiobolus, Penicillium, Rhizopus, Rhodotorula, Saccharomyces, Staphylococcus, Streptomyces, Torulopsis, and Trichoderma or preparations thereof.

12. A process for producing d-threo-2-(piperid-2-yl)-2-phenyl acetic acid comprising bringing a compound of the formula (I): ##STR6## wherein R.sup.3 is cyano, and R.sup.1 and R.sup.2 are hydrogen, into contact with a nitrile hydratase and amidase at least until a substantial amount of said compound is converted to d-threo-2-(piperid-2-yl)-2-phenyl-acetic acid substantially free of the 1-isomer, and recovering said d-threo-2-(piperid-2-yl)-2-phenyl acetic acid or a derivative thereof.

13. The process according to claim 12 wherein the nitrile hydratase is of microbial origin.

14. The process according to claim 13 wherein the nitrile hydratase and amidase are obtained from at least one microorganism selected from the group consisting of Alcaligenes, Pseudomonas, Rhodopseudomonas, Corynebacterium, Escherichia, Arthrobacter, Aspergillus, Acinetobacter, Brevibacterium, Bacillus, Mycobacterium, Rhodococcus, Agrobacterium, Botrytis, Candida, Chaetomium, Chromobacterium, Cladosporium, Enterobacter, Microbacterium, Mucor, Nocardia, Ophiobolus, Penicillium, Rhizopus, Rhodotorula, Saccharomyces, Staphylococcus, Streptomyces, Torulopsis, and Trichoderma or preparations thereof.

15. A process according to claim 12 wherein the unreacted d-threo-2-(piperid-2-yl)-2-phenyl acetamide is recovered.

16. A process for producing d-threo-2-piperid-2-yl)-2-phenyl acetic acid methyl ester comprising bringing a compound of the formula (I): ##STR7## wherein R.sup.1 and R.sup.2 are hydrogen, and R.sup.3 is carboxy methyl, into contact with an esterase at least until a substantial amount of said compound is enriched to d-threo-2-piperid-2-yl)-2-phenyl acetic acid methyl ester substantially free of the 1-isomer, and recovering said methyl ester.

17. The process according to claim 16 wherein the esterase is of microbial origin.

18. The process according to claim 17 wherein the esterase is obtained from a microorganism selected from the group consisting of Alcaligenes, Pseudomonas, Rhodopseudomonas, Corynebacterium, Escherichia, Arthrobacter, Aspergillus, Acinetobacter, Brevibacterium, Bacillus, Mycobacterium, Rhodococcus, Agrobacterium, Botrytis, Candida, Chaetomium, Chromobacterium, Cladosporium, Enterobacter, Microbacterium, Mucor, Nocardia, Ophiobolus, Penicillium, Rhizopus, Rhodotorula, Saccharomyces, Staphylococcus, Streptomyces, Torulopsis, and Trichoderma or preparations thereof.

19. A process for producing a d-threo amide of the formula ##STR8## comprising contacting a racemic amide of the formula ##STR9## with an amide at least until a substantial amount of said racemic amide is resolved to said d-threo amide.

20. A process for producing a d-threo acid of the formula ##STR10## comprising contacting an amide of the formula ##STR11## with an amidase at least until a substantial amount of said racemic amide is converted to said d-threo acid.
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